The 20 Worst Draft Day Trades in NBA History

The 20 Worst Draft Day Trades in NBA History

Over the years, NBA draft day has become the most important day of the offseason for GMs around the league to try and pull off blockbuster deals.

While some have worked out for all parties involved, most draft day trades, like all trades, have a clear winner and loser.

Trades on draft day can be particularly exciting, and particularly complicated. The combination of proven veterans getting dealt, teams moving up to take unproven rookies, and of course the dreaded "future considerations", make every deal that takes place on draft day one that will be of particular interest for fans everywhere for years to come.

Looking back on it today, it may be tough to figure out just what some teams were thinking when they pulled off these head scratching draft day deals that changed the course of NBA history.

The 2012 NBA draft will no doubt feature plenty more draft day trades for us to examine for years to come, when the festivities begin a week from today in Madison Square Garden.

But for now with this year's NBA season officially over, and the 2012 draft on the horizon, let's examine some of the most lopsided deals that took place on draft day in league history.

20. Cavaliers Send Charles Oakley to the Bulls

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Over the course of his career that spanned nearly 1,300 NBA games, Charles Oakley was consistently one of the toughest and most physical power forwards in the league.

Oakley was a one-time NBA All-Star, and averaged nearly a double-double over the course of his time in the NBA, which he split between five teams.

One of those teams however, was not the Cleveland Cavaliers, despite the fact that the Cavs selected Oakley with the 9th overall pick in the 1985 NBA draft.

On draft day, Cleveland sent Oakley to the Bulls for Ennis Whatley and Keith Lee.

Oakley would go on to receive All-Rookie honors in 1986 while playing along side Michael Jordan, before eventually being traded to the Knicks and becoming a focal point of their success in the 1990s along side Patrick Ewing.

Whatley on the other hand averaged only 5.6 PPG over his 10-year NBA career, and Lee lasted only three seasons in the NBA with the Cavs and Nets in the mid-1980s.

19. Chicago Gives Up Brand for Chandler

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Donald Sterling has made dozens of horrible personnel choices during his reign as the owner of the Los Angeles Clippers, but in 2001, he and the rest of the Clipper front office pulled off a rare draft day win when they picked up Elton Brand from the Chicago Bulls for Tyson Chandler and Brian Skinner.

While the trade has certainly looked more even as the years have gone on, there is still no comparing the numbers of Chandler to those of Brand since they both came into the league.

Chandler over the last two seasons has been both a starter on an NBA championship team, and the NBA's Defensive Player of the Year, but he still has averaged only 8.6 points, and nine rebounds since his career started. At his best, Chandler is a great defensive force but will not impact the game much on the offensive end.

Skinner had only one season over the course of his career where he averaged more then 10 points per game, and had not averaged more then four in any season at the time of the trade.

Brand on the other hand was the co-Rookie of the Year in 2000 for the Bulls, and could have been the driving force in turning the franchise around in the post-Michael Jordan era.

Instead he was traded away despite averaging over 20 points per game in both of his seasons with the Bulls. Brand would go on to become a two-time NBA All-Star, and could have gone down as one of the best players of the decade had he not been plagued by injuries throughout his career.

18. Rockets Let Go of Gay for Battier

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With Yao Ming and Tracy McGrady still in their prime, the Houston Rockets in 2006 were desperate to find the right pieces to surround them and turn themselves into an NBA Championship contender.

On draft day, they saw an opportunity and traded away the rights to eighth overall selection Rudy Gay out of Connecticut to the Memphis Grizzlies, for swing man Shane Battier, who they hoped would help them improve defensively and advance deeper into the playoffs.

Battier played well with the Rockets that season averaging over 10 points per game, playing his normal stellar defense, and remaining with the franchise for the next five seasons.

However, his counterpart in the trade Rudy Gay quickly evolved into one of the best players from the entire 2006 draft.

Gay averaged over 20 points per game in 2007-2008, only his second year in the league, and has been the Grizzlies primary scorer throughout his career.

Plus at age 25, Gay still has plenty of room to grow as a player and could easily become a perennial All-Star by the time he hits his true prime as a professional.

The Rockets never did win that elusive Championship, and Battier, Yao, and McGrady have all since moved on.

If they had held onto Gay, not only would they have improved their odds of winning at that time, but would still have something to show for it to this day.

17. Memphis Chooses Mayo over Love

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Deep into draft night in 2008, the Memphis Grizzlies and Minnesota Timberwolves worked out an eight-player blockbuster deal that would see third overall pick O.J. Mayo go to Memphis, while fifth overall pick Kevin Love would head to Minnesota.

The Grizzlies also sent over Mike Miller, Jason Collins, and Brian Cardinal in the trade while the T-Wolves parted ways with Greg Buckner, Marko Jaric, and Antonie Walker.

With no disrespect to those six players, this deal boils down to the Mayo for Love swap, that has gone significantly Minnesota's way thus far.

At the time however, many were heralding the deal as a win for the Grizzlies.

Mayo would join the aforementioned Rudy Gay as a dynamic one-two scoring punch in Memphis, while there was still many questions about how Love's game would transfer to the NBA level.

At best, most saw him as a role player on a contending team who could provide rebounding and the occasional three-pointer.

Instead, Love has turned into a bona fide NBA superstar.

This season, Love averaged 26 points per game, averaged over 13 rebounds, made All-NBA Second Team for Minnesota while finishing sixth in MVP voting.

Mayo, has been a good player during his time in Memphis, but has been inconsistent and does not measure up to what Love has been able to accomplish at age 23.

Needless to say, if the Grizzlies had held on to Love to pair alongside Rudy Gay, they could have had one of the best (and youngest) one-two punches in the Western Conference.

16. Knicks Trade the Franchise for Antonio McDyess

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With players such as Amar'e Stoudemire and Caron Butler still on the board, the New York Knicks instead opted to take Brazilian Center Nene Hilario with the seventh overall pick in the 2002 draft.

While that move in and of itself was a mistake, Nene has still proven to be a productive player in his NBA career and the pick certainly would not have caused too much uproar if he had played the early days of his career in a Knicks uniform.

It was the subsequent move to ship Nene, Marcus Camby, and Mark Jackson to Denver for Antonio McDyess and the No. 25 overall pick that lands the Knicks on the list of worst draft day moves in NBA history.

McDyess was coming off a major knee injury and was nowhere near the player he was in his best years in Denver from 1998-2000.

He would go on to miss the entire 2002-2003 season, and average a mere 8.4 points, and 6.6 rebounds in only 18 games in 2003-04, his only season in New York.

That No. 25 overall pick that the Knicks got from the Nuggets did not exactly pan out either. That picked turned into Frank Williams out of Illinois who accomplished nothing of note in his four NBA seasons.

15. Timberwolves Trade Allen for Marbury

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The 1996 NBA draft is largely considered to be one of the most deep classes in history.

Most experts rank it with the 1984, and 2003 draft classes as among the best classes of all time as it produced players such as Kobe Bryant, Allen Iverson, Steve Nash, Jermaine O'Neal, Marcus Camby, and the two men involved in this draft day trade, Stephon Marbury, and Ray Allen.

The two star guards were chosen back to back with the fourth and fifth selections overall. Marbury out of Georgia Tech, was taken by the Milwaukee Bucks with the fourth overall pick, and Allen out of UConn was taken fifth by the Minnesota Timberwolves.

Later the two teams traded the two players for each other, with the Bucks also receiving a future first-round pick.

In a way it is hard to fault the T-Wolves for wanting Marbury, and it was not as though he did not have a successful NBA career.

Marbury averaged nearly 20 points a game during his 12-year career, and was always among the most talented point guards in the league.

Still, he spent only three seasons with Minnesota after he fell out favor with Timberwolves' management during the 1999 season. Marbury would go on to play in New Jersey, Phoenix, New York and eventually Boston where he was Allen's teammate, but his attitude always got in the way of his talent at every stop he made.

Assuredly, the T-Wolves would not have had that problem had they gone instead with Ray Allen.

Allen would of course go on to become the NBA's all-time leader in three-pointers made, and during his prime with Milwaukee and Seattle was one of the top scorers in the entire league.

Not to mention, Allen is well known throughout the league as being one of the most classy and well liked players in the NBA.

We finally got to see how good Allen and Kevin Garnett could have been together when they teamed up on the Celtics and won an NBA championship in 2008.

14. Suns Miss out on Deng and Igoudala

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In 2004, the Phoenix Suns still had a nucleus of players that included Steve Nash, Amar'e Stoudemire, Joe Johnson, Shawn Marion, and Leandro Barbosa that in retrospect definitely should have won at least one NBA title at some point.

But in the 2004 NBA draft, the Suns had an opportunity to add yet another dynamic piece to their roster with the No. 7 overall pick.

Still in the board at No. 7 were future All-Stars Andre Igoudala and Luol Deng, who would have without a doubt thrived in the Sun's seven seconds or less system and helped them improve defensively.

Instead, the Suns shipped the pick to Chicago for $3 million cash, and a 2006 first-round pick. The Bulls would go on to select Deng who has been a great player for them throughout his career.

So what did the Suns do with that 2006 first-rounder that could have made up for the loss of adding A.I, or Deng to their already stacked roster?

That moves requires a whole different spot on our countdown.

13. Suns Trade Away Rajon Rondo

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As compensation for the No. 7 pick in 2004, the Suns received what turned out to be the No. 21 overall pick in the 2006 draft.

With that pick the Suns selected Rajon Rondo out of Kentucky, and then promptly traded him away to Boston for more cash, and 2007 first-round pick.

On the Suns, Rondo could have been a great change of pace guard off the bench, while learning the tricks of the trade from one of the greatest point guards of all time in Steve Nash.

Instead, he went to Boston, where Rondo figured it all out on his own, and became one of the NBA's best point guards anyway, all the while helping the Celtics win the NBA championship in 2008.

Today, Rondo has surpassed the rest of his "Big Three" teammates and is now the Celtics most prized possession.

But at least the Suns got that 2007 first-round pick out of the whole spiel right? Well not exactly, Phoenix owner Robert Sarver traded that pick in 2007 to Portland for you guessed it, more cash.

12. Portland Misses out on Both Williams and Paul

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With no disrespect to Andrew Bynum, Monta Ellis, Andrew Bogut, or Danny Granger, it is safe to say that seven years later, the two best players to come out of the 2005 NBA Draft, were point guards Deron Williams, and Chris Paul who went three and four overall, respectively.

The Portland Trail Blazers, positioned with the third overall pick, had the opportunity to get to choose between them after Bogut and Marvin Williams went first and second respectively.

Either way they went, Portland would have had their point guard for the future, and assuredly would have positioned themselves amongst the West's better teams for the latter half of the decade.

Instead, Portland traded the pick to the Utah Jazz for the number 6 and 27 overall picks in the draft.

The Jazz went on to take Williams who led them to the playoffs four years in a row, and become a three-time all-star, while the New Orleans Hornets took Paul with the fourth pick, who had even more success before being moved to the Clippers last offseason.

The Trail Blazers used the sixth pick on Martell Webster who did not pan out to be worthy of a lottery selection, and the 27th on Linas Kleiza who never played a game in a Blazers uniform before being traded to Denver.

11. Ray Allen Gets Sent to Boston

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As I mentioned earlier, Ray Allen was one of the NBA's top scorers during his prime in Milwaukee and Seattle.

In 2007, coming off of a season in which he averaged a career high 26.4 points for the Supersonics, Boston Celtics GM Danny Ainge made the first move in creating his "Big Three" that would go on to win the Celtics a championship just a year later.

On draft night, Ainge acquired Allen, as well as the No. 35 pick (Glen "Big Baby Davis) from the Sonics for the No. 5 pick Jeff Green, with Delonte West and Wally Sczerbiak.

The trade allowed Ainge to convince Kevin Garnett to sign with Boston, and along with their previous year's draft day trade that had seen them acquire Rajon Rondo, laid the foundation for what was to become the East's most dominant team for the next three seasons.

While Green (who was eventually traded back to the Celtics by the Oklahoma City Thunder, the former Seattle Supersonics) has had a nice career so far, West is a great off the bench point guard, and Sczerbiak would go on to have a couple more productive years in the league, none of them compare to Allen, even when combined.

While Oklahoma City's futility because of this trade allowed them to draft Russell Westbrook, Kevin Durant, and James Harden and reach the position where they are today, it still does not mean it was a fair trade as Boston got an absolute steal in acquiring Allen.

10. Hawks Pass Up on Pau Gasol

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In the 2001 draft, Pau Gasol, a 7'0'' power forward out of Spain was chosen third overall by the Atlanta Hawks.

If Gasol had remained in Atlanta, he likely could have carried them into the playoffs and been the best player on the franchise for the majority of the decade, just like he did with the Memphis Grizzlies.

Memphis traded for Gasol, as well as Brevin Knight and Lorenzen Wright by giving Atlanta Shareef Abdur-Rahim and the 27th pick in the 2001 draft, which turned out to become Jamaal Tinsley.

Abdur-Rahim was a solid player throughout his NBA career. While playing for the Grizzlies, (they were the Vancouver Grizzlies when he was there) he set the franchise record for points and was the centerpiece of the Grizzlies organization.

However, despite his personal success, he was never able to lead the team to the promised land. In Atlanta, even when being paired along side Jason Terry and Glenn Robinson, Abdur-Rahim was unable to lead the team to the playoffs.

Gasol, went on to play for the Grizzlies for seven seasons, win the Rookie of the Year honors in 2002, become the team's all-time leading scorer (passing the man he was traded for), make the All-Star game in 2006 while playing in a Memphis uniform, and lead the team to their first two playoff appearances.

This is another case of teams swapping good players, but in this case the Hawks opted for the proven Abdur-Rahim instead of the potential of Gasol, and they lost big time.

9. Portland Lands LaMarcus Aldridge

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As the 2006 NBA draft neared, debate raged on as to whether there was more potential in Texas power forward LaMarcus Aldridge, or LSU big man Tyrus Thomas.

Aldridge had a more refined game, but Thomas had off the charts athleticism that many thought would translate better into the NBA game.

After the Raptors selected Italian Andrea Bargnani first overall, the Chicago Bulls went ahead with Aldridge making him the second overall pick in the draft.

With the fourth selection, the Trail Blazers took the next best thing in Thomas, but soon after, the two would swap teams.

On draft night, Portland sent Thomas to the Bulls along with Viktor Khryapa for Aldridge and a future second-round pick.

Since they made their NBA debuts, all Aldridge has done for the Blazers is average at least 17 points per game in every season but his rookie year, make the All-Rookie team, and become an All-Star and All-NBA selection.

Thomas's talent has still not caught up to his athleticism as he has averaged under eight points and five rebounds during his career for the Bulls and Bobcats.

As for the third man in the trade, Viktor Khryapa, he played just 42 games with the Bulls after the trade, averaging under three points and ten minutes played per contest before being bought out and returning to play in his native Russia.

8. Rockets Give Up Jefferson for Eddie Griffin

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Another deal on this list that transpired during the 2001 NBA draft was the acquisition of Eddie Griffin by the Houston Rockets in exchange for Richard Jefferson, Jason Collins, and Brandon Armstrong.

At the time, it seemed like a proverbial slam dunk deal for Houston, as many saw Griffin as the steal of the draft (I feel awful for whoever wrote that piece).

Griffin's high expectations however faded quickly as he battled with depression and alcoholism while never really being able to produce at a high level on the court.

Griffin put up nearly nine points a game his rookie season, but was released from the Rockets in 2003 after missing team practices and a team flight.

Eddie Griffin played his last NBA game in 2007, and died tragically as the result of car crash in August of that year.

Jefferson meanwhile, was a huge success in New Jersey playing a key role (Collins as well) in their trips to the finals in 2002 and 2003 along side Jason Kidd.

While it would have been impossible for the Rockets to know about all of the demons Eddie Griffin was facing, it still goes down as one of the biggest bloopers in team history.

7. Cavaliers Snag Brad Daugherty

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Back in 1986, the Philadelphia 76ers were sitting in one of the most enviable positions in the NBA.

They had Moses Malone, Julius Erving and a young Charles Barkley on their roster already, plus the No. 1 overall pick in the upcoming NBA Draft.

They could have made the pick and taken Len Bias, Brad Daugherty or any number number of players to ensure they would win an NBA Championship.

Instead, they traded the pick to the Cleveland Cavaliers for Roy Hinson and cash. The Cavs in turn used the top pick to take UNC big man Daugherty, and change the direction of their franchise.

Hinson would be traded after just a year-and-a-half with the team, and the 76ers would also trade Moses Malone soon after, only being left to think of what might have been.

Daugherty had an extremely successful NBA career winning the Rookie of the Year in 1987 and becoming a five-time NBA all-star.

Despite being forced to retire at age 28, Daugherty left the game as the Cavaliers all-time leading scorer and rebounder.

Daugherty helped the Cavs obtain a winning record in 10 of the next 12 seasons with the aid of the next man on this list, who Cleveland managed to acquire on the very same night.

6. Cleveland Deals for Mark Price

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Later on in the 1986 draft, the Cavaliers made an under the radar trade that would go onto become the single most-important in franchise history.

They traded a second-round pick in 1989 to the Dallas Mavericks for the rights to Mark Price, the 25th selection in that year's draft.

Pick No. 25 was in the second round back in 1986, so few expected that a player picked so late would have the impact that Price managed to have.

Price was thought by many to be too small, and too slow to have success at the NBA level, but the doubters were quickly proven wrong when Price got to Cleveland.

Along with Brad Daugherty, Price turned the Cavaliers into an Eastern Conference powerhouse in the late '80s and early '90s.

Price was a four-time all-star, and a three time All-NBA performer, even making the first team in 1993. All the while becoming the greatest player in Cavaliers history, pre-LeBron James.

Dallas used the pick they received on their end of the deal to select a player named Jeff Hodge out of South Alabama in the 1989 draft. Hodge never played a game in the NBA.

5. Celtics Trade for Parish and McHale

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The Celtics dynasty in the 1980s was largely centered around the trio of Larry Bird, Robert Parish, and Kevin McHale.

While Bird had joined the club in 1978, the other two players were both acquired by Celtics GM Red Auberbach in the same day, draft night 1980.

Auerbach traded the first and 13th picks in the draft for the third overall selection and four-year veteran Robert Parish of the Golden State Warriors.

Parish had scored at 17 points a game in the previous two seasons for Golden State and was emerging as one of the best big men in the NBA.

The Warriors however, thought that he was worth giving up so they could select Joe Barry Carroll out of Purdue with the first pick and Rickey Brown with the 13th.

Neither had careers comparable to Parish.

Despite having the reputation as a bust, Caroll's numbers with the Warriors were actually very solid. He averaged 19 points per game his rookie season while snagging 9.3 rebounds.

In 1982, Carroll averaged a career high 24.1 points per game, and he made the All-Star team in 1987.

However, Carroll was unable to lead his team deep into the playoffs, never leading the Warriors past the second round.

Brown never scored more than five-and-a-half points per game in his three-year tenure with the Warriors.

Parish would win four NBA championships with the Celtics, score over 23,000 points in his career and become a nine-time all-star.

The Celtics also used the third pick in that draft to pick up Kevin McHale who would go on to be another crucial part of three Celtics NBA Championship teams as well as a seven-time all-star in his own right.

4. Sonics Deal Pippen for Polynice

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Who knows how Michael Jordan would be perceived today if he did not have Scottie Pippen by his side to win his six NBA championships.

Pippen was the Robin to Jordan's Batman and without him, MJ likely would not have won those championships and would not be universally considered to be the greatest basketball player of all time.

So when you think of Michael Jordan, there is one person he should rightfully thank in aiding him in his path to greatness. Olden Polynice.

After all, if it was not for Polynice, Scottie Pippen would have remained in Seattle, and Jordan would have had to do it all by himself.

During draft day 1987, the Sonics traded away Pippen for Polynice and future draft pick considerations.

Pippen would of course as I mentioned go on to win six NBA championships with the Bulls, and would also go on to become a seven-time all-star, three-time First-Team All-NBA performer, and would become one of the 50 greatest players of all time.

Polynice...well he would not do any of those things. In his 15 year NBA career, Polynice averaged 7.8 points and 6.7 rebounds, a serviceable player, but nothing more.

If Pippen had stayed with Seattle, he could have potentially paired up with Gary Payton and Shawn Kemp and who knows how things would have played out.

3. Dallas Scoops Up Dirk from Milwaukee

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Without a doubt, Dirk Nowitzki is the greatest Dallas Maverick in history, and has to be considered one of the top scorers of all time when he decides to hang it up.

However, if Nowitzki had played his career out with the team that had drafted him, he would have been doing it all in a Milwaukee Bucks uniform.

Nowitzki was taken ninth in the 1998 NBA draft by the Bucks, only to be immediately traded to the Mavericks along with Pat Garrity for Robert Traylor.

At the time, Traylor was considered one of the top big men prospects in the NBA but his career never got off the ground.

He battled obesity throughout his entire life before passing away in 2011. He finished his pro career with an average of 4.8 PPG with 3.7 RPG and played only two seasons with the Bucks in his career.

Nowitzki has gone on to become an 11-time NBA all-star, 12-time All-NBA selection, the current 19th leading scorer in NBA history, and finally an NBA Champion and Finals MVP in 2011. Topping off perhaps the most successful career of any foreign born player in NBA history, a title that is rivaled only by Hakeem Oljauwon and Patrick Ewing.

2. Charlotte Sends Kobe to Tinseltown

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Fresh out of high school, 17-year-old Kobe Bryant was drafted with the 13th overall selection in the 1996 NBA draft by the Charlotte Hornets.

However, Bryant made it clear he only wanted to play for one team, the Los Angeles Lakers.

So the Hornets pulled off what had to be considered at the time a pretty good trade for a 17-year-old unproven kid, by having the Lakers send over starting center Vlade Divac to Charlotte, in exchange for Bryant.

Divac had been a great player in his seven years with the Lakers and was coming off his best personal season in which he scored over 16 points per game, and grabbed 10.4 rebounds.

Divac however, would play just two seasons in Charlotte before moving on to Sacramento where he would be a key part of the Kings run towards the top of the Western Conference in the 2000s.

But as good as Divac was, two seasons of him will never ever make up for trading Kobe Bryant.

It is obvious to any NBA fan what Kobe means historically. He is a five-time NBA champion, former MVP, two-time finals MVP, 14-time all-star and simply put the greatest player to play the game since Michael Jordan.

For natives of Charlotte, the NBA just has not been very kind to them. First they lose out on Kobe and now the 2012 Bobcats are the worst team in NBA history. Ouch.

1. Boston Begins a Dynasty with Bill Russell

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Crank up your time vault, because for the No. 1 entry on this list we are going all the way back to the 1956 NBA draft.

Entering the draft, the St. Louis Hawks had control of the No. 2 overall selection and the Rochester Royals had already selected Sihugo Green out of Duquense with the first pick, since they were unwilling to pay the $25,000 signing bonus that was requested by Russell for whichever team drafted him.

The Hawks drafted Russell No. 2 overall, but Boston Celtics head coach Red Auberbach had his sites set on Russell. Auerbach eventually agreed to give up the Celtics best player "Easy" Ed McCauley as well as Cliff Hagan, (a player who had not yet played for the Celtics since he was serving time in the military) in return for Russell.

The move seemed curious to many at the time for Boston to give up McCauley, their best player, on a team who had finished second in the East last season for an unproven Russell. However, the deal would end up going down as one of the most important in the history of North American sports.

Not to mention on the same night in 1956, Auberbach drafted Tom Heinsohn and K.C. Jones who would also go onto have hall of fame careers with the Celtics.

McCauley had an extremely successful Hall of Fame career in his own right, becoming a seven-time NBA all-star and one time champion in 1958.

However, Russell would not bring just one title to the Celtics but actually, 11.

Russell's Celtics won the NBA Championship in his rookie season of 1957, and then would win 10 out of 11 years between 1959 and 1969.

Russell would also go on to become a five-time NBA MVP, and 12-time all-star.

Comparing McCauley to Russell is almost unfair, since no player has been able to accomplish what Russell did in his career.

Still, if the Hawks had held onto Russell in 1957, maybe we would be talking today about the dynasty of the St. Louis Hawks instead of the Boston Celtics.